1. Field of the Invention
The invention concerns anomers of certain novel analogs of spectinomycin including asteric mixtures thereof. The invention also includes novel intermediates for making spectinomycin analogs. Methods of making spectinomycin analogs is also within the invention.
2. Description of the Prior Art
Spectinomycin is a known antibiotic having the formula ##STR1## Heretofore, spectinomycin has been prepared by a microbiological process. See Bergy et al., U.S. Pat. No. 3,234,092.
Some analogs of spectinomycin are described by Rosenbrook Jr. et al., in J. Antibiotics, 28, pp. 953 and 960 (1975) and J. Antibiotics, 31, p. 451 (1978). In addition Carney et al. describes chlorodeoxy derivatives of spectinomycin in J. Antibiotics, 30, 960 (1977). Further 9-epi-4(R)-dihydrospectimomycin is reported by Foley et al., in J. Org. Cehm., 43, 22 pp. 4355-4359 (1978).
However, contrary to the present invention, biological activity is not reported for any of the spectinomycin analogs and derivatives disclosed in the above cited references.
The prior art disclosing chemical processes nearest the invention process teach a preferential reaction at the 5-hydroxyl of 2-deoxystreptamine (1) with tri-O-acetyl-2-deoxy-2-nitroso-.alpha.-D-glycopyranosyl chloride (2) to give a .alpha.-pseudodisaccharide (3) in the following manner (see Lemieux, Can. J. Chem. 51, p. 53 (1973): ##STR2## wherein CBz is carbobenzyloxy. Mallams et al., J. Chem. Soc. Perkin I, p. 1118 (1976), extend the Lemieux reaction to synthesize di- and tri-saccharides.
Removal of oximes is taught by Lemieux et al., Can. J. Chem. 51, p. 19 (1973) and Mallams et al., J. Chem. Soc. Perkin I, p. 1097 (1976).